m-Chloroperbenzoic acid → HCID 12791054, compound

HRID 1413696Notes

Reaction equation

HRID 1413696 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[CH2:5][N:6]([C:30]([S:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:7][P:8]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)=[O:9])[CH3:2].ClC1C=CC=C(C(OO)=[O:49])C=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:40])[CH2:5][N:6]([C:30]([S:32]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:49])=[O:31])[CH2:7][P:8]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1)([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1)=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12791039HCID 12791039, compound

Product 1

HCID 12791054HCID 12791054, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl-N-[(benzylthio)carbonyl]-N-[bis(3-nitrophenoxy)phosphinylmethyl]-glycinate (2.0 g.; 0.0034 mol.) dissolved in 50 ml. of methylene chloride was added metachloroperbenzoic acid (0.69 g.; 0.0034 mol.) at 0° C. The reaction mixture was stirred for 4 hours while allowed to gradually warm to 25° C., then filtered. The filtrate was washed with 5% sodium hydroxide, dried, and concentrated in vacuo to yield ethyl-N-[(benzylsulfinyl)carbonyl]-N-[bis(3-nitrophenoxy)phosphinylmethyl]-glycinate (1.3 g.) as an oil (nD25 =1.5654) having the following analysis:

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 5% sodium hydroxide
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f551e44c15243dc904c50a8326b848c
Source dataset
uspto-grants-1981_02
Patent number
US04251258

Reaction notes

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